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My Awesome Baby-sitter

Author: Ron

Summary: Ian is a fairly typical nine year old boy, even though he has a
bit of a mischievous side that comes out sometimes. His baby-sitter
Sandy, who is now in college, has been baby-sitting him since he was a
baby. What looked to be another normal evening of baby-sitting for Ian
turns out to be quite different due to Ian's sudden feelings toward
wearing diapers again. Ian may just get the chance to revisit his past
and go through an evening of "baby"-sitting.

“IAN, GET UP AND GET READY FOR SCHOOL!”

I woke up with a start. I had been having a dream in which I was an
actual baby wearing a diaper and sleeping in a crib, but now, I was in
neither a crib, a diaper, nor the body of a baby. Instead, I awoke in
the same bed that I went to sleep in the night before, my pajamas and my
normal nine year old body. It was another one of those stupid early
school mornings, and my mom was yelling at me to get up.

Realizing that it was no use trying to avoid getting out of bed, I
slowly rolled out of bed, grumbling at how I hated school. My dream had
been kinda weird, but I couldn’t help but miss it now that it was over.
I couldn’t even remember it that much, except that I was really small
and that I was really happy during it, which could not be said for my
state now that I was awake.

Well, at least this was Friday, so I’d get a couple of days to forget
everything we would do during the school day. I groggily changed into a
T-shirt and jeans before taking a quick look in the mirror. There I was,
my somewhat skinny self, with my brown hair miraculously still in place
after waking up (it came down past my ears all the way around my head
except for my eyes since I wanted to be able to actually see during the
day). After throwing on my socks and tennis shoes, I plodded down the
stairs to the kitchen.

As my mom and dad ate their breakfast and drank their coffee, I put some
Frosted Flakes and milk into a bowl and began eating, still having
trouble keeping my eyes open. It was a rainy day out, and it was early
enough that it still looked pretty dark outside. As I crunched my
cereal, I remembered that it was Friday, and I tried to make the most of
it.

“Hey mom,” I said. “Can I have Brian over tonight? It’s not a school
night.” Brian and I had been best friends since I can remember, and we
had gone over to each other’s houses so many times we both practically
had two addresses.

“Have you forgotten already Ian?” my mom asked me. “I told you that your
father and I are going out to a movie tonight, and Sandy is going to
come over to baby-sit you tonight.”

“And taking care of one little monster is all we’re going to ask Sandy
to do, I don’t want to double her stress level by making her watch both
you and Brian,” my dad added.

‘Oh, that’s right,’ I thought, since (like always) I had forgotten what
mom had told me. Hey, I’ve got other really, really important things to
be remembering. Anyway, since dad was exaggerating me and Brian’s
behavior I felt I had to say something.

“Hey, Sandy loves coming over. I’m her favorite kid!” I retorted.

“Mmm, right,” my dad said. “I personally don’t know how she puts up with
you sometimes. Well, if you behave yourself tonight, then the next time
we’ll see if Sandy will agree to watching both of you. But knowing your
little actions as of late, I don’t know if that will happen.” He gave me
this little “dad” look as he said the last part.

I don’t know what he was talking about. It had been like, two months
since I had done something bad. Ok, maybe it was one week, but you get
what I’m saying. Either way, I still felt pretty good. I always had a
fun time when Sandy came over ‘cause unlike all the girls at school,
Sandy was actually a girl who was cool.

Sandy had been taking care of me ever since I was a baby. I think she
was around thirteen when she started baby-sitting me, and now she was
like, in college, but since her college was really close to her house,
she still lived there and still baby-sat me for some extra money.
Anyway, she was kind of pretty, but she was really athletic, too. She
always liked doing fun stuff, like playing soccer, going roller skating,
and playing video games. She even took karate! The other girls that I
knew (who all went to school with me) liked to do stupid things like
play with dolls and you know, other girl stuff.

As I got my backpack and went to the bus stop, I felt better knowing
that no matter how bad school was that day, I’d at least have a pretty
good time that night.

Even though the day dragged, I did get to see Brian and a couple of the
other boys who were in my class, and it was eventually over. I spent a
couple of hours at home watching TV and playing on my PlayStation 2, and
then around 5:30, I heard a car pull-up. I went downstairs to our door
to go see Sandy as soon as she walked in.

As the person who dropped her off drove away, I saw her walking toward
the house. She was wearing a white blouse and a pair of somewhat tight
jeans, and her long brown hair blew a little bit in the soft breeze. But
something was different about her; she was carrying something over her
shoulder. As she got a little closer, I noticed it was one of those baby
bags that people carry all the baby’s stuff in.

The thought that jumped into my mind immediately was that the baby bag
was for me. I mean, why else would she have it? I started to get kinda
panicked; I thought mom had told Sandy that since I had been bad
recently that I should be treated like a baby. I really started to panic
as she came closer and my heart began to pound in my chest as I got a
picture in my head of my mom and dad holding me down while Sandy took
out a baby diaper and taped it on me (although I will admit that for
some reason I was kinda excited about the idea as well, even though I
didn’t know why).

Without thinking I ran out to Sandy as I felt a lump starting to form in
my throat. As I ran up she said “Hey kiddo, how are you? Ready to have
some fun tonight?” (at the moment I was positive that she was referring
to treating me like a baby).

Immediately my voice turned strangely whiny as I eyed the bag and begged
her, “Sandy, please, please don’t dress me like a baby! I’ll be good, I
swear. I won’t give you any trouble….”

I was cut off by Sandy bursting into a laugh. She had to cup one hand
over her mouth to try to stop herself? What, did she find the idea of
treating me like a little baby funny?

Before either of us could say anything, my mom came out the door and
began to speak. “Hello, Sandy! Hey, what’s so funny?”

As Sandy finally stifled her laugh, she said “Ian, you silly kid! This
diaper bag isn’t for you! I had to baby-sit another family’s baby
before I came over here, silly!”

I felt myself go pink as my mom started to laugh too. As I took in what
she said I realized how extremely stupid I had just been and I felt like
hitting myself in the head very hard.

As my mom calmed herself, she asked Sandy, “What, the Thompsons’ boy? I
didn’t know he was still in diapers.”

“Well, they wanted to potty train him, but he’s having trouble, so they
decided not to push him. These are Pampers size 6 that I’ve got in the
bag. I bought this bag since I baby-sit a few babies in the neighborhood
anyway, and they just told me I can keep some of his diapers in here so
I don’t have to hunt for them in their house.”

“Wow those are pretty big diapers!” my mom said. “I bet those might even
be able to fit Ian!”

“Mom!” I said indignantly as Sandy laughed slightly. It was bad enough
that she had to say things like that at all, but it was even worse in
front of Sandy, especially after what I had just said earlier.

“Well, it’s not like we would have found out before, since little man
here was potty trained real early,” Sandy said as she gestured towards
me (Little man was a nickname that Sandy had called me since I could
remember).

“That is true,” mom said. “But I know you yourself have changed plenty
of Ian’s poopy diapers in the past, Sandy!” she added with a laugh.

“MOM!” I said again as I felt myself blush even more. “Do you have to
say stuff like that?” I don’t know why she always felt she had to do
that.

“Oh come on Ian,” Sandy said. “Your mom’s just kiddin’. Besides, you
were such a cute little baby that I never minded changing your poopy
diapers! In fact, I still think you’re kinda cute.” With the last line
she got me in a headlock and gave me a soft noogie.

“Hey, cut it out!” I said, but this time I was smiling. What she said
didn’t really comfort me, but I always liked it when Sandy played around
with me like that.

Anyway, a few minutes later, mom and dad had gone, and Sandy and I went
in the house, “diaper bag” (as mom and Sandy called the baby bag)
included.

“Alright, Ian,” Sandy said. “Your parents want us to stay here tonight,
so I’m gonna go order a pizza. Why don’t you head on into the living
room and decide what you want to do tonight? Oh yeah, and take the
diaper bag with you. If it’s in the living room I’ll be less likely to
forget it.”

“Alright,” I said, feeling very funny as I took the diaper bag turned
and walked into the living room. After I put it down against the wall, I
decided to plop down on the couch and flipping on the TV. As I watched,
I couldn’t make myself think about what I wanted to do that night; my
mind kept on drifting over what had just happened with mom and Sandy
outside. As I eyed the diaper bag, various images kept on entering my
mind; Sandy saying how she used to change my diapers, mom mentioning
that those size 6 pampers could probably fit me, my imaginary image of
me being forced into a diaper by Sandy again…

The more I thought about it, the more I began to fantasize about wearing
a diaper again. I knew it was pretty silly; I was nine years old after
all, and everyone knew that diapers were only for babies. I mean,
everyone I knew would have died laughing if they saw anyone my age
wearing a baby diaper. But despite this, I couldn’t help but be filled
with a desire to see what it would feel like to wear a diaper again.
Suddenly, I remembered parts of the dream that I had had that morning.
Soon, I was picturing myself lying down on my back, Sandy leaning over
me with a diaper in her hand. In my mind, she remarked how I was such a
cute little baby, and then before I knew it, I had a diaper taped snugly
around my waist.

But it wasn’t just wearing a diaper that was so intriguing to me. To
make things even weirder, I had a desire to wet a diaper too. I just
really wanted to know what it would feel like to just be able to let
loose and feel the warm pee up against my legs and crotch. I could
picture Sandy saying “Did my little baby Ian go pee pee in his diapy?
Alright, kiddo, let’s get that diaper changed…”

Sandy suddenly entered the room, and she startled me a bit as I was
shaken out of my fantasy. She asked me if I what I wanted to do as she
sat down, and she seemed to be surprised that I didn’t have an answer.

“You’re sure acting funny tonight, Ian,” she said. “First you burst out
and think I brought a diaper bag for you, then you jump when I enter the
room, and now you can’t think of anything to do when normally your head
is bursting with ideas.”

“Uh, well, it was kinda, uh, a hard day at school,” I said, forcing
myself to keep my eyes away from the diaper bag leaning up against the
wall.

This seemed to satisfy her, though. We started watching TV and after a
while the pizza arrived and we ate while we watched. Things seemed to be
finally getting back on a normal track again. That is, until something
unexpected began a turn of events that would lead to a very interesting
evening.

“My Awesome Babysitter” Part 2

After we finished our pizza and the drinks we had, we just continued to
watch TV. Had we decided to turn off the TV right then, the evening
probably would have just been normal. But this was not the case because
during one of the commercial breaks, a diaper commercial just happened
to appear on the screen.

Although the commercial was pretty simple, it had a pretty powerful
affect on me. The mother in the commercial gave so much attention and
love to the baby as she changed his diaper. In addition, the speaker in
the commercial kept referring to how soft the diapers were, and they
placed special emphasis as to how stretchy their diapers were. I myself
had never actually been around babies, so I didn’t know much about what
it was like to be around diapers. However, the commercial seemed to draw
me back to the time when I was a baby, and the diapers still seemed
somewhat familiar. As much as I tried to seem uninterested, I couldn’t
keep myself from watching every second of the commercial very deeply and
intently.

I don’t know if Sandy actually noticed this or not, but it may very well
have been the reason that she decided to say something.

“Wow, it’s amazing how far products have come!” she said. “Those diapers
look like they could hold a lot. The stretchiness of those diapers looks
pretty incredible, too. The ones you used to wear weren’t nearly that
flexible. I bet these new ones would not only fit a baby well, but they
might fit you now, Ian!” She even gave a small chuckle with this line.

She then laughed again and said “I wouldn’t even be surprised if they
fit me!”

I still don’t know exactly why I didn’t just laugh along with her and
let the topic rest after that. I guess it was the affect the commercial
had on me, the appeal of the statements she had just made, or that darn
diaper back leaning up against the wall that I just couldn’t keep my
eyes from drifting to. Whatever it was, I just couldn’t stop myself from
pressing the topic even more; the desire to wear a diaper again just
kept popping up in my mind.

“Yeah, I guess it would be pretty neat to be able to put on a diaper
again!” I said with a laugh of my own.

Somehow I knew right after I said it that I may have gone too far.
Although she was still smiling, Sandy stopped laughing when I said this.
She raised an eyebrow as she looked at me and asked, “Uh, why do you say
that, Ian? Wouldn’t it be kinda weird for a nine year old like you or a
21 year old like me to be seen with a diaper on?”

“Uh, right, of course,” I said as I nervously laughed. “It would be
pretty stupid. I mean, uh, I haven’t wanted to wear diapers since I was
a baby. I mean, uh, I haven’t worn diapers since I was a baby, and uh, I
don’t want to now or anything. It’s stupid.” With this, I turned back
toward the TV, trying not to look at Sandy. I felt myself start to go
red again and I knew that she was still looking at me.

“Uh, right, whatever you say, Ian,” she said. I could tell she was still
laughing a little and even though she turned back toward the TV, there
was a bit of a weird tension between us as we started watching TV again.

A few minutes passed with neither of us saying a word, but then she
began to speak again.

“Well, you know, Ian,” she said as she turned toward me again. I looked
at her and she continued by saying “I do have some diapers with me
tonight.” She nodded toward the diaper bag. “They’re pretty big, I bet
they’d fit you no problem. No one would ever know, and you could see
what it would be like to wear one again.”

Without thinking, I excitedly said “Really?!”

“Aha!” Sandy said. “I knew that’s what you wanted tonight!”

“No!” I responded. “No, I was just kidding. I mean, diapers, like,
they’re for babies, right? Why would I wanna wear one?” However, I was
very nervous as I said this, and my voice sounded kinda funny as my body
tensed a little.

“Come on, Ian,” she said, obviously looking past what I had just told
her. “You’ve been acting funny ever since you saw that diaper bag. You
can’t fool me. I know you like to look like you’re a rambunctious little
ball of boy energy, but you can’t help but get excited at the idea of
being put into a diaper again.”

“No, really, I mean it!” I said, although I convinced neither her nor
myself. “That’s crazy!”

“Well, maybe a closer look might make you reveal you’re true feelings.”
With that, she strode over to the diaper bag, reached inside it, and
pulled out one of the size 6 Pampers that she had told mom about. As she
brought it over, I could tell she had been right; even though I knew
nothing about diapers, I could tell that it would fit me no problem.

She sat down and unfolded it a little, making sure to keep it up close
to by body. She even grabbed my hand and made me feel the plastic cover.

As this was happening, a new wave of excitement washed over me. I was
pretty sure that the last time that I had actually touched a diaper was
when I wore them as a toddler, and the sight, touch, and especially
smell of it made my body tingle with excitement.

Sandy apparently noticed something in my reaction, because she looked me
right in the eye and then said, “See? I knew it. Come on Ian, I won’t
laugh, and I definitely won’t tell anyone. You can tell me. Truly,
honestly, would you like to wear diapers again?”

There was something about the way she spoke that made me feel that I
couldn’t help but trust her. I was really embarrassed about telling her
that this is what I so badly wanted, but the look on her face was so
sincere that I decided to just take the plunge and be honest.

“Well, I…..uh, well, yeah,” I said. “It’s just….I don’t know, I just
think it would be really neat to put one on again.”

“Well, what are we waiting for?” she asked. She got up, still holding
the diaper in one hand, and beckoned me over with her other hand. “Let’s
go get you diapered right now!”

Somehow this isn’t quite what I had expected. “Wait a sec…don’t you find
this the slightest bit weird? I mean, I’m assuming you haven’t had the
experience of diapering many nine-year olds.”

“Well, I have to admit, I can’t say I know many people who want to wear
diapers that don’t need them. But so what, you gotta try new things,
right? I was scared to try bungee-jumping, but that was a great
experience! I doubt putting a diaper on a nine-year old will be that big
of a deal.”

This made me feel much better about the whole idea. If Sandy didn’t
think I was crazy for wanting this, then it wouldn’t be so bad. As a
grin spread across my face, I excitedly said “Alright, let’s do it!” I
then bolted past her and raced up the stairs to my room.

Although this caught Sandy off guard, she quickly chased after me. I
heard her yell, “Whoa, slow down little man! Wait for me!”

I stopped once I got into my room so I could catch my breath, but right
after I got there, Sandy appeared in the doorway. She dropped the diaper
on the floor, ran over to me, and playfully threw me down onto my bed. I
smiled as she continued to wrestle with me, holding me down while I
tried to escape her hold on me. She then smiled and said “Calm down,
little man! You gotta lie still if I’m gonna get you into a diaper!”

As I my laughter calmed down, Sandy went over to get the diaper and
threw it onto my bed next to me. “I’m tellin’ you,” she said. “This
reminds me of when you were a toddler. It was quite a job wrestling you
into your diapers every time I had to change you!”

This statement made me turn a little pink, but I had to admit that the
image of Sandy struggling to put a hold my toddler self down in order to
change my diaper was kinda funny.

“Alright, I just want you to relax and let me handle everything,” she
told me. I tried to do this despite my sheer excitement of being put
into a diaper again. Sandy left my shirt on but rolled it up so that my
stomach and chest were visible. She then undid my jeans and slid them
down my legs and off of my ankles. I felt pretty awkward, but I forced
myself to stay relaxed. As she was doing this, it seemed as though Sandy
was somewhat pleased to be doing this whole thing.

“Hey Sandy,” I said. “It seems like you’re enjoying this as much as I
am!”

“Well,” she responded. “Like I said, even if you don’t wanna hear it,
you are a pretty cute kid. And I just think you’d look even cuter
wearing a diaper! Besides, it’s like a bit of nostalgia for me; I’ve
seen you grow from a baby to a kid these past years, and it’s kind of
nice to see you looking, well, like a baby again.”

She then grabbed my underwear and proceeded to pull them off as well. As
she did this, I automatically covered up my privates with my hands,
feeling myself go completely red at the same time.

Sandy giggled when she saw this and just calmly said “Oh Ian, relax,
it’s nothing that I haven’t seen before. Remember, this isn’t the first
time that I’ve put a diaper on you!”

This was pretty much just cold comfort to me, but realizing that I would
have to be naked before Sandy could put a diaper on me, I slowly let my
arms relax at my sides while Sandy finished taking off my underwear.

Sandy then reached for the diaper next to me. As she unfolded it in
front of my face, she said “Alright, little man, one diapered bottom
coming right up!”

“My Awesome Babysitter” Part 3

I was still relaxing my body, but I have to admit that it felt pretty
funny because Sandy then grabbed both of my ankles in one of her hands
and lifted my legs up. I expected her to comment on getting a clear view
of my naked butt in her face, but she said nothing as she slid the
diaper underneath my raised butt. She lowered me down, and before I knew
it, she was already pulling the diaper up over my waist.

Although I still felt somewhat embarrassed about the whole thing, I
couldn’t keep myself from watching what Sandy was doing. Sandy obviously
knew how to change diapers well, because it took her no time at all to
pull the sides of the diaper around my hips and tape up both sides so
that it fit me perfectly. The feeling of the diaper around my waist was
interesting; I have to admit that it felt funny, but it felt oddly
familiar and very pleasing at the same time. The soft and snug feel of
the diaper was very comforting, and somehow feeling the soft material up
against my skin made me feel…safe.

Once I felt it was on, I sat up and looked down at my diapered self to
get a better feel for it. It fit perfectly; in fact, from my viewpoint,
my lower half looked just like the babies that I had seen in those
diaper commercials. The idea excited me greatly, especially since it was
combined with the soft and secure feeling of the diaper up against my
skin. I couldn’t help but simply look at Sandy, smile and say “These
feel…well, really nice!”

“I knew you’d like it!” she said. “Here, get a better look!” she added
as she grabbed me by the wrist and led me over to the mirror in my room.

As I looked at my reflection, I was somewhat awestruck. I lifted up my
shirt so that I could get the full view. The upper half of my body
looked just like it always did, with my brown hair coming down around
the sides of my head and my light blue Myrtle Beach shirt looking just
as normal as ever. But from my belly button down, I looked just like a
toddler. My diaper had a slight bulge in the back, and the cartoon
designs on the front of it clearly made me feel little. Despite the fact
that I still felt a little silly and embarrassed, I still found my
reflection somewhat cute.

Anyway, I still loved the feeling and look of the diaper, and I felt
like I never wanted to take it off. Before I could take in more about my
diaper, Sandy picked me up, placed an arm around me, and walked out the
room carrying me on her hip (I was pretty light, I guess, plus like I
said, Sandy was pretty athletic).

“Come on, little man, let’s go back downstairs.” Although I was caught
off guard when she did this, I didn’t object. I had no desire to put my
pants back on, I was happy in only my diaper and shirt. Besides, it had
been a while since Sandy had picked me up and carried me like this, and
to be honest, I kinda missed it.

Sandy put me back down on the couch downstairs, and then said, “How
‘bout a little music, little man? You like rock music, right?”

“You bet I do!” I said.

She went over and flipped the radio on to the most popular rock station
in our town. I had recently really gotten into listening to music, and I
liked rock the best. I didn’t really know the bands, but I liked a lot
of the songs that I heard on the radio. Immediately I listened up, and
they were playing one of my favorite songs. I got up from the couch and
got into the song. Before we knew it, both me and Sandy were singing
along with the music. We even danced and did a little air guitar. I was
having a blast and the fact that I was wearing a diaper even slipped
from my mind.

Well, until Sandy suddenly stopped in the middle of another song, that
is. She apparently got a case of the giggles and couldn’t stop laughing.

“What?” I asked giving her a puzzling look.

“I’m sorry, Ian, but I just realized, you used look just like you did
when you were a toddler. You used to do the exact same thing; you’d get
up and dance to music in just your shirt and your diaper with a big
smile on your face. And everyone watching would always say how adorable
you looked and laugh. And it is true, you do look just adorable dancing
around in your diaper.”

I felt myself really start to blush when she said this. For some reason,
I didn’t want to be wearing a diaper anymore. I just felt like a little
baby and was very embarrassed at the idea of everyone laughing at me
dance around in a diaper. I went over to the couch and sat down, a big
frown spread across my face.

“Hey, Ian…” Sandy began, but I didn’t want to hear it. I was nine years
old, I wasn’t a baby anymore, and I didn’t want to have anyone remarking
about how cute I looked in diapers. The more I thought about how I had
these desires to wear diapers, the more I was bothered by it.

“Come on, little man,” she said. “I didn’t mean anything by it…”

I felt tears beginning to form in my eyes. “I’m not a baby!” I told her.
“I don’t need diapers! I don’t wanna be the cute little baby that
everyone thinks is helpless and needs diapers! I’m nine years old, and…”

Sandy put her arms around me and began to hug me. “Oh Ian, I know that,”
she said. “I know you’re not two anymore. I know you’re a big boy now,
and I don’t have to change you diapers anymore.”

“So why do I like this?” I asked her. “Why did I want to put on a diaper
tonight?”

“Well, I don’t know exactly, Ian,” she said. “But you know what? It
doesn’t matter. I know, I know I keep telling you how cute you look, but
you’re still nine, even if you do like the idea of wearing diapers. But
so what? I don’t think it’s a bad thing. I mean, I know tons of old
people who forget what it’s like to be young anymore, and let me tell
you, they’re no fun at all, they’re just completely boring. You’re still
really young, but at least you can find happiness in remembering what it
was like when you were younger. Most people just forget all of the
things about them when they were toddlers, and you haven’t yet. And I
think that’s pretty darn cool, personally.”

“Really?” I asked.

“Yeah,” she said. “You did beat me in soccer last week, remember? And
you’re a pretty tough fighter, even if you are wearing a diaper,” she
added with a grin.

“Yeah!” I said. I then felt something; I had to pee. Automatically, I
got up to go the bathroom.

“Hey, where are you going?” Sandy asked.

“To the bathroom,” I replied, not giving it a second thought.

“Now wait a minute,” she said, as she grabbed my arm. “What exactly do
you think that thing around your waist is for?”

I suddenly remembered my diaper and felt kinda funny. “Wait, you don’t
expect me to uh, you know…uh, in my, in my…”

“Yes, your diaper,” she said. “Come on Ian, put up your dukes!” she said
and she lunged at me and playfully tackled me to the ground.

My automatic response was to fight back. “Oh, you’re on now!” I said as
I began to smile and pummel her with my fists.

But then she started to tickle me, and I’ve always been real ticklish. I
was helpless to stop her, no matter how fast I tried to move my hands.
Even worse, the pressure on my bladder had increased greatly, and I
didn’t know how much longer I could hold it in.

“That’s the idea, silly!” she remarked. “Come on, little man, I wanna
see you go pee pee in your diapy!”

I was laughing so hard that I didn’t even get embarrassed by this
comment. Instead, my body just gave way; before I knew it, I started
peeing without any ability to stop it.

But the diaper did it’s job; instead of me feeling my pee trickle down
my legs, I felt my private area and my thighs get warm and moist as my
bladder emptied. To my surprise, it was the best feeling in the world;
my laughter combined with the warm feeling made me feel extremely happy,
and even any embarrassment I had about wetting myself didn’t make me
feel bad at all.

Somehow Sandy could tell that I had done it, because she stopped
tickling me. “There, that wasn’t so bad now, was it?” she asked as my
laughter died down.

Even though I was a little embarrassed to admit it, I told her that it
actually felt pretty good. She apparently didn’t think this was weird
because she just gave a small laugh and then changed the subject.

“Well, you know what, little man, it’s gettin’ pretty late, and your
parents will be home soon. And they’ll kill me if they see that you’re
still up. So back upstairs you go!”

She picked me up again and carried me back up to my room. She again told
me to just lay down on the bed and relax. She then left and came back
with a damp washcloth.

Although I didn’t really want to take off my wet diaper, I knew I had no
choice, so I gave no objection as Sandy un-taped it and took it off. She
then began to wash my private area with the washcloth, and yet again, my
natural reaction made me pull away from her.

“Oh, come on now, Ian,” she said with a smile. “I can’t send you to bed
dirty like this, and I know I can clean you off faster than you can.”

“Oh, all right then,” I said resentfully. However, even though I
wouldn’t admit it to her, it felt amazingly good to have her wash me
down there.

She gave me my underwear and pajamas. She then told me to put them on,
brush my teeth, and get in bed. Although I would normally protest to
these commands given my mischievous nature, I was tired out from our
activities and didn’t feel like arguing. As I did this, I saw Sandy put
my wet diaper into the diaper bag, and she carried it downstairs. By the
time that she was back, I had already dressed and brushed my teeth. She
decided to tuck me in, and she kissed me on the forehead as she
whispered “I had fun tonight. And no matter how big you get, you’ll
always me my ‘little man’. And I know you’ll never forget I’m still the
one who can change your diapers.”

I thought maybe I would have been embarrassed by this, but I wasn’t; I
actually just felt so special that I couldn’t think of anything to say
back. I laid there thinking about the evening as Sandy went turned off
the light and left the room.

“My Awesome Babysitter” Part 4

Throughout the rest of the weekend I thought a lot about what had
happened when Sandy had come over. I could hardly believe that Sandy had
actually diapered me, and on top of that, I actually wet it. It
was so amazing that I couldn’t help but get excited when Mom told me
that Sandy would be baby-sitting for me again the next Friday. And for
the first time ever, when Mom asked if I wanted to have Brian over that
night (I had been good for Sandy, and that was the deal, right?), I told
her no. As much as I liked Brian, the thought of being diapered again
was too exciting.

The week dragged on even more than it normally did, and by the time
Friday rolled around I was bursting with excitement. I was not let down,
because there Sandy was again with the diaper bag around her shoulder.
Sandy even explained to Mom that she would probably have the diaper bag
with her for the next few weeks because she was still baby-sitting the
kid being potty trained (good cover story on her part).

It actually was kinda awkward when my parents left that night. I hadn’t
seen Sandy for the first time in a week, so there was a weird tension
between our normal routine and the fact that last week had been very
different, what with me being diapered and all. As much as I wanted to
jump right back into where we left off the week before, I had trouble
telling Sandy that I wanted her to diaper me again.

“So, little man,” she said. “What’s up?” (it was weird, she said this
almost as if the previous week had never happened).

“Uh, not much,” I responded. “It’s been kind of a boring week.”

“I wish I was you,” she said. “Not only have I had a ton of schoolwork,
but me and Chad have been having some issues.” (Chad was her boyfriend).

Even though my mind kept thinking about diapers, I listened to what she
had to say. However, at the end, I couldn’t contain myself any longer,
so I took the plunge.

“Uh, Sandy?” I asked. “Do you think, you know, if you don’t mind, could
you, uh, I mean…”

“Let me guess,” she said with a small laugh. “You want me to put you in
another diaper, right?”

“Well, yeah,” I admitted with a shy sort of smile.

“Ok then kiddo,” she said with a smile of her own. “I thought that would
be what you wanted. Luckily, I came prepared, and I might just have some
surprises for you. Well, if you don’t mind the floor, why don’t we just
take care of business right here in the living room?”

“Oh! Yeah, that’d be great!” I said.

“Alright, since I don’t want to make a mess on the carpet, take off your
pants and lie down on this changing pad.”

She took out this little mat thing and put it on the ground. I felt
kinda weird getting naked again, but not as weird as the week before. As
I took off my pants and underwear, I saw Sandy take out a diaper and a
couple of other things.

I lay down on the pad feeling weird but also very excited. Sandy didn’t
unfold the size 6 Pamper right away; instead, she first took this small
bottle that said “Baby Lotion” on it.

“Ok, now this might feel a little weird, but babies should have lotion
on them before they’re diapered.”

Noticing the look on my face, she then said, “Oh come on Ian, I know
you’re not really a baby. But if I’m gonna diaper you, we’re gonna have
to do it MY way, ok?

I nodded my head even though I wasn’t crazy about the idea. I was
beginning to feel more and more like a baby again. On the other hand,
part of me liked this idea.

It was definitely pretty weird having Sandy put the baby lotion in her
hand and massage it into my private area as well as my butt. But I knew
that this is what she did to the babies whose diapers she changed, and
plus it felt pretty good.

She then took out a little canister of baby powder. “I don’t want my
little man to get a diaper rash, now do I?” she said with a sly little
grin. As she lifted my legs up and shook the baby powder on my butt I
felt a great sense of joy; the baby powder smelled wonderful and I got
another little jolt of excitement as I was reminded even more of when I
was a baby.

Sandy then took the diaper and slid it underneath my butt. She lowered
me onto it, sprinkled some more baby powder onto my front, and before I
knew it, had fastened the diaper around my waist snugly. As I got up, I
felt extremely happy and well, cute, just like a baby.

As Sandy put away the baby supplies, she beckoned me over to the couch
and patted it, telling me to sit down.

After I did so, Sandy looked at me seriously and began to speak. “Ok,
Ian, listen up, because this is serious. Last week gave me a few ideas,
and to be honest, I find you absolutely adorable in your diapers. But
since I’ll probably never get this chance again, and because I like you,
I want your full cooperation tonight. The deal is, you do what I say, no
questions asked. If you refuse, I’ll tell your parents all about you
wearing diapers again, and I’ll act like you took them and wore them on
your own.”

She saw the shocked look on my face, and then said, “I know Ian, but I
really don’t want to have to do that. All I ask is your full and total
cooperation. If you don’t want to do this, tell me now, and I’ll take
that diaper off of you and we’ll have a ‘normal’ evening. Otherwise, the
deal is on. So what do you say?”

I have to admit I was kinda confused about all of this. What did Sandy
have in store, and why was it so serious to her? I was definitely a
little surprised as well, so I needed a chance to think about it. As
cool as Sandy was, I didn’t doubt for one second that she’d tell my
parents I had taken the diapers on my own, and they’d no doubt believe
her given my past actions. I was kinda nervous about giving Sandy
complete control of me. But my diaper felt so good that I didn’t want to
take it off. And besides, it was Sandy, and I trusted her.

“Ok,” I said. “I’ll do it. You have full control.”

“Excellent!” she said. “Alright Ian, remember, full cooperation, no
‘buts’. But don’t worry, if it really gets to be too much for you, just
yell ‘Stop!’, and the diaper goes off and the evening will be normal.
Got it?”

“Got it,” I said, feeling good that I had a way out, but feeling nervous
that things could get so bad I’d need to yell stop.

“Alright then, let’s start by changing your clothes. Don’t worry,” she
said seeing the look on my face. “That diaper isn’t going anywhere until
it needs to be changed into a new one. However, I want you to take off
your shirt.”

As I did this, I saw her pull an article of clothing out of the diaper
bag: it was one of those one-piece set of pajamas for babies, which I
later learned was called a footed sleeper. However, it was bigger than
one for a baby; in fact, it looked just the right size for me.

This definitely surprised me. I mean, diapers were one thing, but now
Sandy wanted me to wear baby clothes as well? Why was she so intent on
this, and what was the point?

I didn’t have much more time to ponder it, however, since Sandy then
told me to lay down again and relax. As I laid down in just my diaper,
she told me to let her do all of the work, so I continued to relax as
she began to put me in the sleeper. I felt kind of silly and even more
like an actual baby, but our deal was still fresh in my mind, so I made
no objection. And after Sandy zipped it up, I had to admit, I actually
liked the feel of it. It made me feel warm on both the outside and the
inside. I felt a smile go across my face as I imagined being little
again, especially since I could feel the padding on my feet as well.

Before I knew it, Sandy had scooped me up in her arms and carried me,
well, like a baby across to the couch. My legs were across one of her
arms and my back over the other. As she sat down, she used one arm to
support my head and I felt my body resting in her lap. I still felt a
little funny but I was very comfortable as well.

While still holding me, I saw her reach into the diaper bag and pull out
a baby bottle full of milk. She was still supporting my head with one
arm and used the other hand to move the nipple of the bottle toward my
mouth. As it came close, I pushed it away and said, “Hey! I don’t wanna
drink from a bottle like a little baby!”

“Wha…” I began to say, but I was cut off as she pushed the nipple into
my mouth. But I remembered our deal and just began to quietly suck from
it. It was just normal milk, and even though it was hard to get out at
first, I actually began to enjoy it. It was very relaxing, and I began
to feel very warm and cozy as I felt the warm cloth over my body,
Sandy’s soft body that I was lying in, and the soft padding of my diaper
on my butt.

I closed my eyes as I continued to nurse from the bottle, and I began to
imagine myself as a real baby again. The feelings that I felt were so
real and before I knew it I felt joy wash over my body. This was
enhanced even more because Sandy begin to talk baby talk to me, saying
things like “Now that’s a good wittle baby. Drink da whole bottle like a
good boy!” This was wonderful, and at that moment I didn’t want to be
anywhere else.

Eventually, the bottle ran out, and Sandy took it out of my mouth. I
opened my eyes and saw her reach down and pinch my cheek saying, “Oh,
little Ian, you’re just adorable.” I felt a smile go across my face as
she said this.

My stomach felt a little funny, but before I could say anything, Sandy
already knew what to do. Before I knew it, she stood up, put me over her
shoulder and began to pat my back. Soon after, I felt the taste of milk
in my mouth as I let out a burp. Sandy had just burped me!

She then shifted me over to her hip. She reached into the diaper bag
once again and this time she pulled out a pacifier. She popped it into
my mouth, which for some reason I didn’t object to at all and began to
suck happily. She laid me down on the couch and I felt myself relax,
allowing all of my baby feelings to just soak in.

Sandy then pulled out a little stuffed teddy bear and told me to hold
it. I did so, and instead of feeling embarrassed or weird, I was just
reminded of when I was little and used to carry around stuffed animals
all of the time.

As I lay there, Sandy sat down next to me and began to softly run her
fingers through my hair. This soothed me even more, and by the look on
her face, Sandy was enjoying it as well.

I then realized that I needed to pee. Remembering that I was diapered
and how good it felt last time, with only a little effort I managed to
get a little trickle going. Soon, I had completely let myself go and
felt the warm moisture up against my legs and waist as my diaper filled.

Sandy must have been an expert baby-sitter, because she already began to
notice. “Uh-oh,” she said in a babyish voice. “Looks like someone has a
wet dydee! We better get him changed!”

With that she lifted me off of the couch and back onto the changing mat.
I was still sucking my pacifier and clutching my bear. I simply
continued to relax as I felt Sandy undo my sleeper and remove my wet
diaper. I got a little shock as I felt something cold touch my private
area; Sandy had begun to clean me with a baby wipe! Within a short
period of time Sandy had cleaned my entire butt and private area, and
after quickly applying some more powder, she taped a new diaper on me
and fastened my sleeper back up.

Afterwards, she told me to sit up and take out my pacifier. She then
began to speak.

“So, what do you think?”

“Wow!” I told her. “This is amazing! Kinda weird at first. And I do feel
a little silly to be sucking a pacifier and drinking from a bottle, but
it feels….well…nice.”

“I thought you’d like it,” she said. “But you see, I don’t think it
would be as good if I didn’t have control of you like that. It wouldn’t
be as real.”

As I began to think about it, what she said was true. With Sandy in
control of me, I didn’t have a care in the world, just like a real baby.

“Well,” she said. “Our time’s just about up, little man. Time for you to
go to bed.”

Sandy then helped me out of my sleeper and my diaper, and she put up all
of the baby stuff as I changed back into my normal clothes. As the
evening ended, I began to think about mom’s offer of having Brian over.
My mischevious mind began to work, and suddenly my head was filled with
an idea for my good buddy.

“Hey Sandy,” I said. “How’s about next week you baby-sitting me AND
Brian…

“My Awesome Babysitter” Part 5

Turns out things would be even more interesting than I had originally
thought. Mom told me that the next Friday night that she and dad would
actually be spending the night away, and Sandy had agreed to sleep at
our house and watch me until Saturday evening. When I asked mom if it
would be all right if Brian came over too, she gave in and said that it
would fine as long as it was fine with Sandy (hey, for two weeks in a
row I had been good for Sandy, right?) I offered to call Sandy and ask
her, and mom agreed. I thought a bit more about what Sandy and I could
do with Brian, I called Sandy and let her know about my plans. I was a
little surprised; not only was Sandy fine with all of my ideas, she was
actually pretty excited about them. I don’t know, maybe Sandy had found
a new love for diapering nine year olds or something.

Anyway, I talked to Brian about him coming over and spending the night
that Friday, and like usual, he was happy to come over.

“Yeah, that sounds cool,” he said. “Sandy’s always been cool when I’ve
gone over there in the past, even when we weren’t really good for her.
Oh yeah, are you up for maybe pulling another trick on her? It would be
all in fun, she wouldn’t get mad.”

“Oh, I think a trick this weekend would be a great idea,” I said. I
never said who the trick would be played on, however.

Friday night came, and Brian just rode the school bus and got off on my
stop. We actually had some fun before Sandy got there, playing around on
the computer and my PlayStation 2. And even when Sandy got there, the
evening played out normally. My plans for Brian would take place the
next morning, and even we were having so much fun with her that he never
even brought up wanting to play a joke on her.

When it was time to go to bed, after we got in bed, Sandy got the ball
rolling for what we were going to do.

“Ok Brian,” she said. “I just want to make sure. You’re not a
bed-wetter, are you?” (she had never watched him overnight, so it was a
fair question).

He looked a little embarrassed to be asked this, and immediately
responded by saying, “What? No! Of course not!”

“It’s ok,” she said. “If you are, it’s nothing to be embarrassed about.
I just want to know.”

“No, really, I’m not!” he said, looking even more uncomfortable. I knew
he didn’t wet the bed, but if someone asked me, I would have felt weird
too.

“Ok, that’s fine. But I’m not washing wet sheets, so if I find out in
the morning that you’re lying, there’s gonna be a big problem, ok?”

“Honestly,” he said. “I’m not a bed-wetter. It’s not gonna happen.”

“Ok. Well, good night, boys.”

With that, she left the room. Me and Brian started talking, and he
asked, “What’s with her?”

“Well,” I said. “She just wants to make sure. She asked me the same
thing the first night she watched me. And since you don’t wet the bed,
you don’t need to think anything else about it.”

Ok, before I go into what we actually did to Brian, you might read it
and think it’s pretty mean. But hey, he had embarrassed me at school a
few weeks ago, claiming he didn’t mean anything by it and that it was
all in good fun. Well, this was just my way of getting him back, and it
was also all in good fun.

Anyway, after we talked a bit more, we got tired and fell asleep.
However, about 8 o’clock the next morning, I felt Sandy wake me up. She
had used an alarm clock to get up, and she told me to keep quiet so I
wouldn’t wake Brian up. She had with her a bowl of warm water.

We didn’t bother with the whole dipping the hand in warm water gag.
Instead, being very careful, Sandy lifted up Brian’s blanket and lightly
poured the water over Brian’s crotch. Luckily he didn’t wake up. As we
both giggled, she told me to pretend I was asleep and get ready because
she would be coming in to wake us up.

As I lay back down and closed my eyes, I heard Sandy leave and then come
back in and yell “Alright, boys, I know it’s Saturday, but you gotta get
up!”

As I acted like I had just gotten up, I felt Sandy yank my blanket off
of me (I had slept on the floor and given Brian my bed). I gave a fake
yawn as I looked over at Brian, who still held his own blanket tightly
so that he didn’t have to get up.

“Ok, Brian, you too,” she said. She continued to speak as she pulled his
blanket off to. “Come on, if we have to get up…” she paused as she
looked down at the wet spot around his crotch and on the sheets. I
looked at her face and saw a look of puzzlement, almost disgust.

Brian then looked down at the wet spot and a look of complete shock
crossed over his face. He opened his mouth but no sound came out, and he
looked at Sandy, then me, and then back at the wet spot.

“BRIAN!” Sandy yelled. “You TOLD me you were not a bed wetter!” I began
to see some anger in her face.

“But…but…I’m not!” Brian said. His voice was shaky and I could tell he
was embarrassed.

“I can’t believe it!” she said. “Well, I have washed too many wet sheets
in the past, and if you’re going to lie to me, I’m just going to have to
punish you for it!”

“No, really,” he started to say. He actually sounded like he was about
to cry. “I didn’t mean to…”

But Sandy would not have it. “I told you there would be a big problem if
I found a wet bed. So you’re just going to have to face the
consequences, Brian. Ian, you come with me, and if you don’t do as I
say, you’ll face the same punishment as Brian.”

Her voice was dead serious, and then she turned and left. I gave Brian a
nervous glance and said “Dude, you never told me you were a bed wetter.”

“Well,” I said. “This is the one thing Sandy is really, really serious
about. I’m sorry, but I’m can’t disobey her, she’s too mad. I’ll have to
do what she tells me.”

Brian looked a little scared now as he realized even I wasn’t on his
side. I then left the room and talked with Sandy.

Even though we knew we were being mean, we laughed a little about what
had just happened. She asked me if I was ok with going on with it, and
even though I felt bad for making Brian upset like this, I remembered
very well how badly he had embarrassed me before, so I decided that I
still wanted to mess with him some more. What I still couldn’t believe
is that Brian actually believed that he had wet the bed; I guess it had
happened so fast that he didn’t realized that it was water and not pee
on his crotch.

Anyway, as Sandy got ready, I went back into the room where Brian was.
Looking nervous, I said, “I’m sorry, Brian, but I’ve got to help Sandy
punish you. If I don’t she’ll punish me, too. So, I just have to
say…sorry”

Brian looked even more nervous, and I think he wanted to try and leave
the room. But at that moment Sandy entered. She closed the door, and
then said, “Well, considering the clothes you’re wearing now are a mess,
we’ll have to take them off. So take off all of your clothes right now
unless you want ME to take them off.”

Brian just merely said “No way! I don’t have any other ones, and I’m not
getting naked here!”

But Sandy said, “Don’t worry about your other ‘clothes’. But if you
won’t take your clothes off, I guess I’ll have to. Ian, get over here
and help me.”

With that, Brian tried to make a break for it, but Sandy simply caught
hold of his wrist and pulled him towards her. While she held him in
place, I first removed his shirt, then his wet pants. As Sandy held him
in his underwear, she remarked, “Well, since you’re not cooperating,
I’ll just have to have Ian tie you down.”

Brian struggled as hard as he could, with a look of mixed anger, fear,
and helplessness on his face. But Sandy held him still, and I took a
piece of rope that I had had in my room and tied one of his wrists to
the head of my bed. I did the same with his other wrist. I tried to make
it look like I didn’t really want to do it. Sandy then let go of him,
and we both looked at him trapped on my bed.

Realizing how he could now do nothing, Brian looked like he was about to
cry. “What are you going to do to me?” he asked weakly.

“Don’t worry, little Brian,” Sandy said as she took off his underwear.
“Your punishment will simply be fitting. If you’re going to wet the bed,
we’ll just have to make it so that this will not be a problem anymore.
Come on Ian, let’s get ready.”

As we walked out of the room, Sandy and I just smiled at each other.
Call me a horrible friend, but I kind of enjoyed taking control of
Brian. I knew at the end of it all we’d just tell him it was a joke, and
for now, payback was all I wanted.

“Ok, Ian, last chance to back out,” Sandy said. I told her that I still
wanted to go on with it, so she picked the diaper bag that had our
supplies in it.

Sandy and I went back into my room. Brian didn’t really have any
response to the diaper bag; well, until Sandy pulled out a size 6
Pampers diaper, that is. It took a few seconds for Brian to register
what it was, but once he did, a new look of fear crossed his face.

“Geez, Brian, calm down,” Sandy said as she began to unfold the diaper.
“It’s not like anyone can hear you anyway, and I’d rather not have to
gag you.”

When Brain heard the word “gag” he seemed to calm down. However, as
Sandy unfolded the diaper completely and started to walk towards him,
his reaction went from anger to pleading.

“Please,” he said, tears now in his eyes. “Please, please, please don’t
put that diaper on me. I’m not a baby!”

“Well, you did go pee pee on yourself last night, and since babies do
too, they need diapers. So, since you acted like a baby, I’m going to
treat you like one. I am a “baby” sitter, after all.”

Brian then began to kick his legs furiously, but Sandy grabbed both of
his ankles in one hand (admittedly, Brian wasn’t the biggest kid). She
asked me for a towel, and after I handed it to her, she put it
underneath him. She then asked me for the baby powder, and I gave it to
her, again trying to look like I was sorry for Brian.

I could see him sobbing now as Sandy began to powder his butt and crotch
area. The smell of the baby powder filled the room, and funnily enough,
the twitching of Brian’s struggling body made him look even more like a
real baby. I even began to feel genuinely sorry for him, but I had
decided that I wouldn’t back down now.

Next, Sandy placed the diaper underneath Brian. She pulled down his legs
over it, pulled it between his legs, and tightly taped both the sides
around his waist.

“There,” she said, dusting her hands off. “That diaper will make sure
that the baby doesn’t make any more messes on the sheets. But we don’t
want ‘baby’ Bwian to be hungry, now do we? You just wait, sweetie, Sandy
will get you all fixed up.”

Sandy then left me in the room with Brian. There he was, lying on the
bed with tears running down his cheeks, diapered just as much as he was
when he was a baby.

Through his tears he said, “Ian, please, I’m begging you, make her stop!
I don’t want to wear a diaper…I’m not a baby!”

But I just sadly shook my head and told him that I had no choice. Soon
after, Sandy came back in, now with a baby bottle full of milk in one
hand. This made matters even worse for Brian, and he then begged her not
to make him drink it.

Sandy, however, would have none of it, and before either me or Brian
knew it, she had shoved the bottle into his mouth. As he was forced to
drink it, the tears continued to pour down his face, and Sandy just made
it worse for him by condescendingly cooing him and saying things like
“Good baby, drink your whole bottle.”

Once he had finished the whole thing, she took it out of his mouth and
put it aside. Then, to my surprise, she just busted out laughing.
Realizing that the joke was now over, I myself began to giggle. I mean,
Brian really had looked kind of funny wearing a diaper and being
bottle-fed.

As we laughed, Brian look confused, but still embarrassed and as he
sobbed, he asked, “What, you guys think this is funny? Putting a…a diaper
on me, and…”

“No, no, Brian, you don’t get it,” Sandy said between laughs. “This
whole thing was a joke that Ian and I came up with!”

“That’s right,” I said as I began to untie him from the bed. “You didn’t
really wet the bed, we just poured some water on you. And I just wanted
to get you back from when you embarrassed me so bad a while back. I was
trying to think of the best way, and I remembered that Sandy always had
some diapers…”

I suddenly remembered that I couldn’t tell Brian about me wearing
diapers. “…for one of the babies that she takes care of. We came up with
the idea of Sandy being really angry with you for wetting the bed and
forcing you into a diaper.”

As I finished untying Brian, he took all of this in. Relief spread over
his face as he realized that Sandy didn’t really think she needed to
baby him. Once he fully took it in, he then got mad at me.

“You jerk!” he said. “How could you do this to me?! To your best friend?”

“Hey man,” I replied. “Don’t forget how horrible I felt after you
embarrassed me last time!”

Unfortunately, this didn’t solve the problem, and he was still very
angry at me. I didn’t know what to do; I hadn’t expected him to be this
mad, and I began to feel bad about what we had done.

Sandy sensed the tension between the two of us, but thankfully, she had
an idea. Without warning and to my great surprise (and Brian’s), she
grabbed me and pinned me to the floor.

“Ok Ian,” she said, her face about an inch away from mine. “Your turn!
Brian, get me another diaper!”

I saw an evil grin spread over Brian’s face as he now realized it was my
turn to be diapered. After the extreme humiliation he had gone through,
this would be sweet revenge for him. As he turned away, Sandy smiled at
me and whispered, “Come on, Ian, play along, this is your chance to be
diapered while Brian is over, and it will make him feel a lot better.
He’ll never know you like it if you act like you don’t!”

Realizing her logic, I calmed down a bit. Even though I was kind of
embarrassed to be diapered in front of Brian, I was also really excited
because I didn’t think that I would get the chance to wear a diaper this
weekend. Plus I couldn’t think of any other way to make him calm down.
However, I knew that I couldn’t let Brian realize that I liked it, so I
tried to look horrified as I saw him come over with the diaper.

Sandy instructed Brian to take my clothes off. I kind of put up a fake
struggle, and I even falsely begged Sandy and Brian not to do it. But
then the inevitable happened…Sandy powdered my butt and before I knew it
I was in a diaper again. Brian was clearly enjoying himself and even
joined Sandy in baby-talking me while she did her work.

Sandy even went the extra mile with me; not only was did I have to drink
from the bottle, but Sandy carried me like a baby while I sucked on a
pacifier. They even tickled me and “forced” me to wet my diaper. Even
though this surprised Brian, he loved it and used it as a great
opportunity to say things like “Aww, wittle Ian wet his diapy and needs
a change!”

The logic behind all of this was beautiful. Although I admit it was hard
to act like I was humiliated (because I was so happy), I loved every
second of my baby treatment. I even think the fact that Brian joined in
treating me like a baby made it even better. But he was having a ball
making fun of me, too. Funnily enough, even though he thought he and
Sandy were playing a joke on me, in reality, we were playing a joke on
him, considering only the two of us knew that I was loving my babyish
state.

However, the joke could only last so long. Sandy put the game to an end,
and after I got out of my diaper, I could tell Brian was much happier.
He had forgiven me for what Sandy and I had done. We then both just
laughed at ourselves and how funny we had looked in diapers.

Soon it was about time for my parents to be back. Sandy made us swear
that we wouldn’t tell anyone about what had happened this weekend (not
that we wanted to anyway). She then said “Bye bye my cute little baby
boys,” as she left us. Right after my parents walked in and had a brief
talk with Sandy. She then left, and it was time for Brian to go too.
After they had both gone, I just relaxed and thought about everything
that had happened that day.

Oh yeah, just in case you’re wondering what Brian had done to embarrass
me so badly, there’s no way I’m telling you. If you think being forced
into a diaper is bad, you have no idea the humiliation I suffered from
Brian’s previous stunt.

“My Awesome Babysitter” Part 6

After Brian and I had our crazy baby-sitting experience, the week-end
was soon over and I was off to school again for the week. I couldn’t
bring myself to mention anything about it to Brian, and he must have
felt the same way because he carried on as if the whole thing had never
happened.

I was fine with this at first; we still were “normal” friends, and we
continued to have a good time with each other and our other friends at
school.

The problem was that Sandy wouldn’t be coming over again for a long
time; she was really busy with her schoolwork among other things, and
the few times my parents decided to go out over the next six weeks, they
just had me stay over at Brian’s or another friend’s house.

This wasn’t a big deal at first, but after the first couple of weeks, I
started going through diaper withdrawal. I couldn’t stop thinking about
how happy I had been wearing and wetting diapers, and I even liked the
thought of seeing Brian in one. My desire became continually strong, and
it got to the point that I had trouble concentrating in school (which
led to a couple of occasions of me looking completely stupid because our
teacher would ask a question and I would be completely clueless as to
what she was talking about). I began to feel like I was going crazy.

What made it that much worse is that I had no one to talk to about it. I
wasn’t able to get a hold of Sandy, and other than her, no one knew that
I had worn a diaper since I was a baby.

Except…Brian. But the fact that he never mentioned anything about it
clearly showed that he was not interested at all. He might have even
forgotten that the whole thing even happened. The idea of me even
mentioning diapers again was weird, and for me to tell him that I
actually enjoyed wearing them was simply preposterous.

On the other hand, I felt that if I didn’t tell anyone about it, I would
explode. I began to picture in my mind how I would tell him and how he
would respond. I wondered if he would think I was really weird or
stupid. I wondered if he would tell anyone else. Most importantly I
wondered if he would still be my friend.

After giving it much thought, I finally decided that I would tell him.
We had been best friends for so long that I felt I could tell him
anything, and I trusted him enough not to tell anyone.

Since I would be going over to his house again the upcoming week-end, I
decided that would be the best time to tell him. I thought about it a
lot that week, and I was very nervous and afraid that he’d laugh at me
or think I was really weird. Still, I stayed resolved to it, and
realized that I couldn’t back out.

Once that Friday evening came, I waited until after we had finished
having dinner with his family to tell him. As we walked up the stairs to
his room, I started feeling slightly sick to my stomach as I began
building up my courage to tell him.

As we got into his room and threw ourselves down on the floor, he
noticed that I looked kinda funny.

“Ian, are you ok? You look a little sick or something.”

I took a deep breathe in and said, “Look, Brian, I got something I have
to tell you.”

Not thinking it was a big deal, he said, “Ok…go ahead.”

“No, it’s really really serious,” I told him. “You have to swear that
you won’t EVER tell ONE single person about it.”

He paused for a second and looked very interested in what I had to say.
A couple of seconds later he said, “All right, I swear, I won’t tell
anybody. We’re best friends, remember?”

As I remembered that he was indeed my best friend, I took another deep
breathe, and said, “Ok, here goes. Remember about a month ago when you
came over to my house, and Sandy was baby-sitting us…”

As he recalled what happened, he smiled a little and said, “Oh yeah…ha
ha, wow, that crazy girl actually put diapers on us! Pretty
embarrassing, huh? I tried to make myself forget about it, but I still
remember how scared I was and how funny it felt to wear a diaper again.”

Feeling a knot beginning to form in my throat, I nervously continued.
“That’s the thing,” I said. “You know when she put the diaper on me?
Well, that wasn’t the first time that I had worn a diaper.”

“Of course it wasn’t, doofus,” Brian said to me with a smile. “You wore
them when you were a baby. I did too. Everyone does. I think I even
slightly remember back when we were in diapers.”

“No, no, that’s not what I mean,” I said, feeling my nerves reach a
peak. “I actually wore one a few weeks before you came over. Sandy put
one on me.”

As I saw his mouth drop, I felt it would be easier if I just kept
talking. Before I knew it, I began blurting out all my feelings about
diapers and being treated like a baby. Brian simply didn’t say anything
and looked like he was having trouble breathing as his jaw dropped and I
launched into the story of how I had seen Sandy’s diaper bag, how she
had offered to diaper me, how I had loved it so much, and how the next
week she had proceeded to treat me like a baby. As I continued, the knot
in my throat became tighter and tighter and I felt more and more queasy.
Brian’s look of shock did not wear off, and I noticed my voice was very
strained and nervous. By the end, I even noticed that I had tears in my
eyes.

“…and that’s where we got the idea to pull a joke on you and put a
diaper on you. Sandy surprised me when she decided to diaper me, but I
was faking when I acted like I didn’t like it. I simply LOVED it, even
though I still don’t get why.”

As I finished, Brian just continued to look at me in disbelief. He
opened his mouth to say something, but then closed it again.

Not knowing what else to say, I just blurted out, “Yeah, I know, it’s
really stupid and weird and you probably think I’m a freak, but you
don’t understand, I’ve been thinking about this for weeks and weeks and
I just had to tell some…”

But Brian then cut me off, and to my great surprise I noticed that he
had tears in his eyes. “Ian, I just simply don’t believe it.”

‘Here it comes,’ I thought. ‘He’s going to lay it on me and say he
doesn’t want to be friends any more.

But I soon realized that they were tears of joy, because he said, “I
never expected this. IAN, I FEEL THE EXACT SAME WAY! When Sandy powdered
and diapered me, I was embarrassed, but a part of me just loved the
whole experience. I loved the smell of the baby powder and the soft feel
of the diaper. I even loved the helplessness of being tied down. But I
didn’t want you guys to know, so I acted really mad about the whole
thing. But ever since then, it’s all that I’ve been able to think about.
But I could never tell you. You’d just think that I was dumb.”

Not believing my ears, the nervousness simply drained from my body and a
wide smile went across my face. It was at that point that I knew that
Brian and I would be best friends for life. But it got even better,
because Brian then said,

“My desires got so bad that I couldn’t take it anymore. I rode my bike
to the grocery store and bought a pack of Pampers Size 6. I was really
nervous about it, but I was able to sneak them home without my parents
noticing. I’ve been wearing them every night and I’ve even wet them! And
getting rid of them isn’t a problem; I just put them in the garbage can
outside and the garbage man takes them away every morning. It’s the best
thing ever!”

With that, he got up and locked his door. He then went over to his
closet. After he rummaged through it for a few seconds, he emerged with
an opened pack of size 6 Pampers diapers.

Excitedly I jumped up and said, “Well what are we waiting for?”

A broad smile spread across his face and he said, “Ok, but me first!”

He quickly took off all of his clothes while I got a diaper out of the
pack and unfolded it. We had seen each other naked before, so it wasn’t
really that weird to see him naked. It was weird, however, for me to
diaper my best friend. Being an only child, I had never diapered anyone,
so it was new to me. But I soon figured out how, and just like that I
had taped up Brian’s diaper and said, “There! All done, mister!”

It was quite a sight. Brian always did look kind of young, what with his
straight blond hair, skinny body, and blue eyes. To be honest, he
actually looked a lot like a real toddler as he lay there in his diaper.

“Ok, now let me do you,” he said with a smile. Within minutes I had
stripped as well and he diapered me. He even gave me a playful pat on my
diapered butt and said “There you go kiddo!” (hey, it’s not that weird,
football players do it all the time, right?)

We continued to play around in our diapers. We first acted like babies
for a bit, and when that got old, we watched a movie in his room. His
parents came up to check on us at one point, but we simply put our other
clothes on over our diapers and his parents never knew. Part way through
the movie, I had to pee, so I naturally decided to go in my diaper (Wow,
I even thought peeing in my diaper was natural). After I let go, I told
Brian about it.

He looked at me and said, “Well, I guess we better change baby Ian into
a new didee!”

I just laughed, put on a babyish voice and said, “Uncle Bwian, will you
pwease change me?” I then smiled at him and put my thumb in my mouth.

“Sure thing!” he said. I kept my thumb in mouth as he changed me into a
fresh diaper, hiding the wet one in his closet.

After I was changed, I noticed that he was wet as well, and I said,
“Uh-oh, looks like someone else had an accident in his diapy, too!”

He just sheepishly smiled and said, “Me go pee pee! Need a new diapy!
Waaaaaa!”

As I laughed I had him lie down and changed him into a new diaper too.
Unfortunately, we heard his mom coming, and after putting our clothes
back on over our diapers, she came in and told us that it was time for
bed. As we got ready for bed, we decided to keep our diapers on. As I
fell asleep that night, I couldn’t think of a time in my life where I
had been happier.

I didn’t get much of a chance to talk to Brian the next morning before I
had to go, and since we didn’t want to arouse any suspicion, we decided
not to mention anything else about the diapers.

Over the next few weeks Brian and I were extremely careful about talking
about our new common interest. Thankfully we got another chance to have
fun in our diapers, and I even gave Brian some money to buy a couple of
baby things like a baby bottle and a pacifier. I found an old teddy bear
and baby blanket to take over to his house, too. We had a very good time.

Thankfully (and somewhat surprisingly), no one ever found out about all
of this. And once Sandy’s schedule lightened up, we convinced our
parents to let her baby-sit both of us again on many occasions. She was
shocked but delighted when she learned about how Brian liked diapers and
being treated like a baby, and we had many fun evenings being babied by
her.

And the greatest thing about it was that Sandy always gave a good report
about our behavior, which meant that our parents trusted us more, and we
got even more opportunities for Sandy to baby-sit us (hey, it gave them
more opportunities to get away from us little monsters). But they were
always surprised to hear that two kids who usually were the most
troublesome ones on the block actually behaved and were “as peaceful as
good little babies” when ever Sandy took care of us.